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4102-53-8 Usage

General Description

4-Iodo-2,6-dimethylaniline is a chemical compound that consists of an aniline group substituted with two methyl groups and an iodine atom. It is commonly used as a building block in the synthesis of various organic compounds, including pharmaceuticals, dyes, and agrochemicals. 4-Iodo-2,6-dimethylaniline has a wide range of industrial applications due to its versatile reactivity and stability. It is important to handle 4-Iodo-2,6-dimethylaniline with caution, as it can be harmful if ingested, inhaled, or comes into contact with skin or eyes. Additionally, its use and disposal should comply with environmental regulations to prevent its adverse effects on the environment and human health.

Check Digit Verification of cas no

The CAS Registry Mumber 4102-53-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,1,0 and 2 respectively; the second part has 2 digits, 5 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 4102-53:
(6*4)+(5*1)+(4*0)+(3*2)+(2*5)+(1*3)=48
48 % 10 = 8
So 4102-53-8 is a valid CAS Registry Number.
InChI:InChI=1/C8H10IN/c1-5-3-7(9)4-6(2)8(5)10/h3-4H,10H2,1-2H3

4102-53-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Iodo-2,6-dimethylaniline

1.2 Other means of identification

Product number -
Other names 4-iodo-2,6-dimethyl-aniline

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:4102-53-8 SDS

4102-53-8Synthetic route

2,6-dimethylaniline
87-62-7

2,6-dimethylaniline

4-iodo-2,6-dimethylaniline
4102-53-8

4-iodo-2,6-dimethylaniline

Conditions
ConditionsYield
With Iodine monochloride In methanol; dichloromethane at 20℃;99%
With In(OSO2CF3)3; Iodine monochloride In dichloromethane; acetonitrile at 20℃; for 1h;98%
With C10H14N4*Cu(1+)*I(1-)*ClI In acetonitrile at 20℃; for 10h; Reagent/catalyst;98%
2,6-dimethylaniline hydrochloride
21436-98-6

2,6-dimethylaniline hydrochloride

4-iodo-2,6-dimethylaniline
4102-53-8

4-iodo-2,6-dimethylaniline

Conditions
ConditionsYield
With iodine; calcium carbonate In water at 60℃; for 0.833333h;92%
2,6-dimethylaniline
87-62-7

2,6-dimethylaniline

A

4-iodo-2,6-dimethylaniline
4102-53-8

4-iodo-2,6-dimethylaniline

B

4-(2,6-dimethylphenylimino)-2,6-dimethylcyclohexa-2,5-dienone
24596-20-1

4-(2,6-dimethylphenylimino)-2,6-dimethylcyclohexa-2,5-dienone

Conditions
ConditionsYield
With hydrogenchloride; sodium iodine dichloride In methanol; water at 20℃; for 3h; pH=1 - 2;A 21%
B 28%
1,3-dimethyl-5-iodo-4-nitrobenzene
144991-54-8

1,3-dimethyl-5-iodo-4-nitrobenzene

4-iodo-2,6-dimethylaniline
4102-53-8

4-iodo-2,6-dimethylaniline

Conditions
ConditionsYield
With ethanol; ammonium chloride; zinc
2,6-dimethylaniline
87-62-7

2,6-dimethylaniline

A

4-chloro-2,6-dimethylaniline
24596-18-7

4-chloro-2,6-dimethylaniline

B

4-iodo-2,6-dimethylaniline
4102-53-8

4-iodo-2,6-dimethylaniline

Conditions
ConditionsYield
With 1-butyl-3-methyl-pyridinium dichloroiodate at 80℃; for 2h; Time; Reagent/catalyst;A 95 %Chromat.
B 98 %Chromat.
4-iodo-2,6-dimethylaniline
4102-53-8

4-iodo-2,6-dimethylaniline

butyraldehyde
123-72-8

butyraldehyde

(4-iodo-2,6-dimethyl-phenyl)-dipropyl-amine

(4-iodo-2,6-dimethyl-phenyl)-dipropyl-amine

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane100%
4-iodo-2,6-dimethylaniline
4102-53-8

4-iodo-2,6-dimethylaniline

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

2,6-dimethyl-4-[(trimethylsilyl)ethynyl]aniline
926895-24-1

2,6-dimethyl-4-[(trimethylsilyl)ethynyl]aniline

Conditions
ConditionsYield
With piperidine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In various solvent(s) at 20℃; for 16h; Sonogashira cross-coupling reaction;100%
4-iodo-2,6-dimethylaniline
4102-53-8

4-iodo-2,6-dimethylaniline

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

N-(4-iodo-2,6-dimethylphenyl) p-toluenesulfonamide

N-(4-iodo-2,6-dimethylphenyl) p-toluenesulfonamide

Conditions
ConditionsYield
With pyridine at 0℃; for 2h;95%
4-iodo-2,6-dimethylaniline
4102-53-8

4-iodo-2,6-dimethylaniline

phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

diethyl (4-amino-3,5-dimethylphenyl)phosphonate
1421533-53-0

diethyl (4-amino-3,5-dimethylphenyl)phosphonate

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); triethylamine In toluene for 12h; Reflux; Inert atmosphere;90%
4-iodo-2,6-dimethylaniline
4102-53-8

4-iodo-2,6-dimethylaniline

para-thiocresol
106-45-6

para-thiocresol

2,6-dimethyl-4-(p-tolylthio)aniline

2,6-dimethyl-4-(p-tolylthio)aniline

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate; ethylene glycol In isopropyl alcohol at 80℃; for 96h;88%
4-iodo-2,6-dimethylaniline
4102-53-8

4-iodo-2,6-dimethylaniline

Acetic formic anhydride
2258-42-6

Acetic formic anhydride

4-iodo-2,6-dimethylformanilide
1210812-13-7

4-iodo-2,6-dimethylformanilide

Conditions
ConditionsYield
In tetrahydrofuran at -20℃; for 0.25h;87%
4-iodo-2,6-dimethylaniline
4102-53-8

4-iodo-2,6-dimethylaniline

4'-ethynyl-2,2':6',6-terpyridine
149817-60-7

4'-ethynyl-2,2':6',6-terpyridine

2,6-dimethyl-4-[2,2';6',2'']terpyridin-4'-ylethynyl-phenylamine

2,6-dimethyl-4-[2,2';6',2'']terpyridin-4'-ylethynyl-phenylamine

Conditions
ConditionsYield
With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide at 20℃; for 20h;85%
bis(tetrabutylammonium) hexamolybdate

bis(tetrabutylammonium) hexamolybdate

4-iodo-2,6-dimethylaniline
4102-53-8

4-iodo-2,6-dimethylaniline

C6H2IN(CH3)2(Mo6O18)(2-)*2(CH3(CH2)3)4N(1+)=(C6H2IN(CH3)2(Mo6O18))((CH3(CH2)3)4N)2

C6H2IN(CH3)2(Mo6O18)(2-)*2(CH3(CH2)3)4N(1+)=(C6H2IN(CH3)2(Mo6O18))((CH3(CH2)3)4N)2

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In acetonitrile Reflux;80%
4-iodo-2,6-dimethylaniline
4102-53-8

4-iodo-2,6-dimethylaniline

4-azido-2,6-dimethylaniline

4-azido-2,6-dimethylaniline

Conditions
ConditionsYield
With copper(l) iodide; sodium azide; Vitamin C; N,N-dimethylethylenediamine; sodium hydroxide In water; dimethyl sulfoxide at 50℃; for 4h; Inert atmosphere; Schlenk technique;79%
4-iodo-2,6-dimethylaniline
4102-53-8

4-iodo-2,6-dimethylaniline

1-(6-(1-((2,6-diisopropylphenyl)imino)ethyl)pyridin-2-yl)ethan-1-one

1-(6-(1-((2,6-diisopropylphenyl)imino)ethyl)pyridin-2-yl)ethan-1-one

2-[1-(4-iodo-2,6-dimethylphenyl)iminoethyl]-6-[1-(2,6-diisopropylphenyl)iminoethyl]pyridine

2-[1-(4-iodo-2,6-dimethylphenyl)iminoethyl]-6-[1-(2,6-diisopropylphenyl)iminoethyl]pyridine

Conditions
ConditionsYield
With silica/alumina In toluene at 45 - 50℃; for 24h; Schlenk technique; Inert atmosphere; Molecular sieve;78%
4-iodo-2,6-dimethylaniline
4102-53-8

4-iodo-2,6-dimethylaniline

A

3,5-dimethylphenyl iodide
22445-41-6

3,5-dimethylphenyl iodide

B

1,4-diiodo-2,6-dimethylbenzene
4102-48-1

1,4-diiodo-2,6-dimethylbenzene

Conditions
ConditionsYield
Stage #1: 4-iodo-2,6-dimethylaniline Diazotization;
Stage #2: iododediazotisation;
A n/a
B 75%
2,6-Pyridinedicarbonyl dichloride
3739-94-4

2,6-Pyridinedicarbonyl dichloride

4-iodo-2,6-dimethylaniline
4102-53-8

4-iodo-2,6-dimethylaniline

1,1-bis(4-amino-3,5-dimethylphenyl)cyclohexane
22657-66-5

1,1-bis(4-amino-3,5-dimethylphenyl)cyclohexane

C52H52I2N6O4
900780-74-7

C52H52I2N6O4

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃;75%
2,6-Diacetylpyridine
1129-30-2

2,6-Diacetylpyridine

4-iodo-2,6-dimethylaniline
4102-53-8

4-iodo-2,6-dimethylaniline

C25H25I2N3

C25H25I2N3

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene Heating;75%
hexamolybdate

hexamolybdate

4-iodo-2,6-dimethylaniline
4102-53-8

4-iodo-2,6-dimethylaniline

C6H2IN(CH3)2(Mo6O18)(2-)*2(CH3(CH2)3)4N(1+)=(C6H2IN(CH3)2(Mo6O18))((CH3(CH2)3)4N)2

C6H2IN(CH3)2(Mo6O18)(2-)*2(CH3(CH2)3)4N(1+)=(C6H2IN(CH3)2(Mo6O18))((CH3(CH2)3)4N)2

Conditions
ConditionsYield
In acetonitrile Kinetics; molybdate/aniline/DCC at 1:1:1 molar ratio; under N2 in refluxing MeCN for ca. 12 h; single crystal X-ray diffraction;72%
ferrocenylzinc(II) chloride

ferrocenylzinc(II) chloride

4-iodo-2,6-dimethylaniline
4102-53-8

4-iodo-2,6-dimethylaniline

2,6-dimethyl-4-ferrocenylaniline
884843-65-6

2,6-dimethyl-4-ferrocenylaniline

Conditions
ConditionsYield
tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran (N2); using Schlenk techniques; stirring at room temp. overnight in the presence of Pd(PPh3)4; (J. Am. Chem. Soc. 1968, 90, 1878); (Polyhedron 1999, 18, 1815); removal of solvent under vac.; chromy. (silica gel);72%
Glyoxal
131543-46-9

Glyoxal

4-iodo-2,6-dimethylaniline
4102-53-8

4-iodo-2,6-dimethylaniline

N,N'-bis(4-iodo-2,6-dimethylphenyl)ethane-1,2-diylidenediamine
1051398-53-8

N,N'-bis(4-iodo-2,6-dimethylphenyl)ethane-1,2-diylidenediamine

Conditions
ConditionsYield
With formic acid In methanol; water Inert atmosphere;71%
With formic acid In ethanol; water at 20℃;68%
With formic acid In ethanol; water at 20℃; for 17h;60%
4-iodo-2,6-dimethylaniline
4102-53-8

4-iodo-2,6-dimethylaniline

acrylonitrile
107-13-1

acrylonitrile

trans-3-(4-amino-3,5-dimethylphenyl)acrylonitrile
500292-94-4

trans-3-(4-amino-3,5-dimethylphenyl)acrylonitrile

Conditions
ConditionsYield
With palladium 10% on activated carbon; tetrabutylammomium bromide; sodium acetate; tris-(o-tolyl)phosphine In N,N-dimethyl acetamide at 140℃; for 12h; Inert atmosphere;69%
tris(4-ferrocenylphenyl)boroxine

tris(4-ferrocenylphenyl)boroxine

4-iodo-2,6-dimethylaniline
4102-53-8

4-iodo-2,6-dimethylaniline

(ferrocenyl)(C6H4)(C6H2Me2)NH2
1210811-86-1

(ferrocenyl)(C6H4)(C6H2Me2)NH2

Conditions
ConditionsYield
With K2CO3 In water boroxine, 4-iodo-2,6-dimethylformanilide reacted in DMF/water in presence of Pd(PPh3)4; chromy. on silica gel (eluent CHCl3/ether); elem. anal.;65%
With K2CO3 In water; N,N-dimethyl-formamide boroxine, 4-iodo-2,6-dimethylaniline reacted in DMF/water in presence ofPd(PPh3)4 and K2CO3; chromy. on silica gel (eluent CHCl3/ether); elem. anal.;55%
1-(6-(1-(4-bromo-2,6-dimethylphenylimino)ethyl)pyridin-2-yl)ethanone
896712-63-3

1-(6-(1-(4-bromo-2,6-dimethylphenylimino)ethyl)pyridin-2-yl)ethanone

4-iodo-2,6-dimethylaniline
4102-53-8

4-iodo-2,6-dimethylaniline

2-[1-(4-iodo-2,6-dimethylphenyl)iminoethyl]-6-[1-(4-bromo-2,6-dimethylphenyl)imino-ethyl]pyridine

2-[1-(4-iodo-2,6-dimethylphenyl)iminoethyl]-6-[1-(4-bromo-2,6-dimethylphenyl)imino-ethyl]pyridine

Conditions
ConditionsYield
With silica/alumina In toluene at 45 - 50℃; for 24h; Schlenk technique; Inert atmosphere; Molecular sieve;58%
4-iodo-2,6-dimethylaniline
4102-53-8

4-iodo-2,6-dimethylaniline

A

3,5-dimethylphenyl iodide
22445-41-6

3,5-dimethylphenyl iodide

B

2-chloro-5-iodo-1,3-dimethylbenzene

2-chloro-5-iodo-1,3-dimethylbenzene

Conditions
ConditionsYield
Stage #1: 4-iodo-2,6-dimethylaniline Diazotization;
Stage #2: chlorodediazotisation;
A n/a
B 56%
2-acetyl-6-[1-((2,6-dimethylphenyl)imino)ethyl]pyridine
395656-36-7

2-acetyl-6-[1-((2,6-dimethylphenyl)imino)ethyl]pyridine

4-iodo-2,6-dimethylaniline
4102-53-8

4-iodo-2,6-dimethylaniline

2-[1-(4-iodo-2,6-dimethylphenyl)iminoethyl]-6-[1-(2,6-dimethylphenyl)iminoethyl]-pyridine

2-[1-(4-iodo-2,6-dimethylphenyl)iminoethyl]-6-[1-(2,6-dimethylphenyl)iminoethyl]-pyridine

Conditions
ConditionsYield
With silica/alumina In toluene at 45 - 50℃; for 24h; Schlenk technique; Inert atmosphere; Molecular sieve;56%

4102-53-8Relevant articles and documents

Immobilization of volatile and corrosive iodine monochloride (ICl) and I2 reagents in a stable metal-organic framework

He, Jun,Duan, Jingjing,Shi, Huatian,Huang, Jian,Huang, Jiahong,Yu, Lin,Zeller, Matthias,Hunter, Allen D.,Xu, Zhengtao

, p. 6837 - 6843 (2014)

The major discovery here is a robust and water-stable metal-organic framework (MOF) material capable of reversible binding of the volatile and reactive molecules of ICl and I2. The immobilization of I2 and ICl, as well as their controllable release thus achieved, is to facilitate the wide-ranging applications of these volatile species as catalysts and reagents in chemical and industrial processes. The framework material TMBP·CuI (hereafter TCuI) can be conveniently prepared in quantitative yields by heating CuI and the organic linker TMBP (3,3′,5,5′- tetramethyl-4,4′-bipyrazol) in acetonitrile. The microporous three-dimensional net of TCuI features CuI chains that contribute to efficient and reversible binding of ICl and I2 molecules, to result in the stoichiometrically well-defined adducts of TCuI·ICl and TCuI·I2, respectively. Moreover, the confinement of a volatile compound like ICl within the MOF medium provides unique opportunities to enhance its reactivity and selectivity as a chemical reagent, as is exemplified by the iodination reactions examined herein. With this exemplary study, we intend to stimulate interest in further exploring MOFs and other porous media (e.g., porous polymers) for entrapping ICl and other volatile reagents (e.g., Br2, SCl2, S2Cl2, and SOCl 2) and for potentially novel reactivity associated with the porous medium.

Imidazolinium-based Multiblock Amphiphile as Transmembrane Anion Transporter

Mori, Miki,Sato, Kohei,Ekimoto, Toru,Okumura, Shinichi,Ikeguchi, Mitsunori,Tabata, Kazuhito V.,Noji, Hiroyuki,Kinbara, Kazushi

, p. 147 - 157 (2020/12/11)

Transmembrane anion transport is an important biological process in maintaining cellular functions. Thus, synthetic anion transporters are widely developed for their biological applications. Imidazolinium was introduced as anion recognition site to a multiblock amphiphilic structure that consists of octa(ethylene glycol) and aromatic units. Ion transport assay using halide-sensitive lucigenin and pH-sensitive 8-hydroxypyrene-1,3,6-trisulfonate (HPTS) revealed that imidazolinium-based multiblock amphiphile (IMA) transports anions and showed high selectivity for nitrate, which plays crucial roles in many biological events. Temperature-dependent ion transport assay using 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) indicated that IMA works as a mobile carrier. 1H NMR titration experiments indicated that the C2 proton of the imidazolinium ring recognizes anions via a (C?H)+???X? hydrogen bond. Furthermore, all-atom molecular dynamics simulations revealed a dynamic feature of IMA within the membranes during ion transportation.

AN IMPROVED ONE POT, ONE STEP PROCESS FOR THE HALOGENATION OF AROMATICS USING SOLID ACID CATALYSTS

-

Page/Page column 0047; 0048, (2019/04/18)

The present invention disclosed an improved one pot, one step process for halogenation of compound of formula (II) to afford corresponding halogenated compound of formula (I) having improved yield and increased selectivity under very mild conditions.

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